GB1071478A - Dinitroaniline derivatives and herbicidal compositions containing them - Google Patents

Dinitroaniline derivatives and herbicidal compositions containing them

Info

Publication number
GB1071478A
GB1071478A GB7814/65A GB781465A GB1071478A GB 1071478 A GB1071478 A GB 1071478A GB 7814/65 A GB7814/65 A GB 7814/65A GB 781465 A GB781465 A GB 781465A GB 1071478 A GB1071478 A GB 1071478A
Authority
GB
United Kingdom
Prior art keywords
dinitro
trifluoromethylaniline
alk
pentyl
compounds
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB7814/65A
Inventor
Quentin Francis Soper
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Eli Lilly and Co
Original Assignee
Eli Lilly and Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Eli Lilly and Co filed Critical Eli Lilly and Co
Priority claimed from NL6503535A external-priority patent/NL139218B/en
Publication of GB1071478A publication Critical patent/GB1071478A/en
Expired legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
    • A01N33/18—Nitro compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/48—Separation; Purification; Stabilisation; Use of additives
    • C07C67/60—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention relates to compounds of the general formula <FORM:1071478/C2/1> in which R is hydrogen, C1-C3 alkyl, C1-C3 haloalkyl, or halogen; and alk is a secondary C3-C7 alkyl group free from quaternary carbon atoms. Compounds claimed per se are: N-(sec.-butyl) - 2,6 - dinitro - 4 - trifluoromethylaniline, N - (2 - pentyl) - 2,6 - dinitro - 4 - trifluoromethylaniline, N - (3 - pentyl) - 2,6 - dinitro - 4-trifluoromethylaniline, N - (3 - pentyl) - 2,6-dinitro - p - toluidine, N - (3 - methyl - 2 - butyl)- 2,6 - dinitro - 4 - trifluoromethylaniline. The compounds may be prepared by heating a primary amine of the formula H2N-alk with an aromatic halide of the general formula <FORM:1071478/C2/2> in the presence of a solvent and preferably in the presence of a strongly basic tertiary amine as hydrogen halide acceptor.ALSO:Herbicidal compositions comprise as active ingredients a compound of the general formula: <FORM:1071478/A5-A6/1> in which R is hydrogen, C1-C3 alkyl, C1-C3 haloalkyl, or halogen; and alk is a secondary C3-C7 alkyl group free from quaternary carbon atoms, together with solid or liquid carriers. Fertilisers may also be incorporated in the compositions. Many examples of active ingredients are given.
GB7814/65A 1963-10-07 1965-02-23 Dinitroaniline derivatives and herbicidal compositions containing them Expired GB1071478A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US314510A US3332769A (en) 1963-10-07 1963-10-07 Method of eliminating germinating and seedling weed grasses and broadleaf weeds
DE1542755A DE1542755C3 (en) 1963-10-07 1965-03-18 Weedkillers based on 2,6-dinitroaniline derivatives
NL6503535A NL139218B (en) 1963-10-07 1965-03-19 PROCESS FOR PREPARING A 2,6-DINITROANILINE DERIVATIVE AND A PREPARATION CONTAINING SUCH DERIVATIVE.
US48506065A 1965-09-03 1965-09-03

Publications (1)

Publication Number Publication Date
GB1071478A true GB1071478A (en) 1967-06-07

Family

ID=27436820

Family Applications (1)

Application Number Title Priority Date Filing Date
GB7814/65A Expired GB1071478A (en) 1963-10-07 1965-02-23 Dinitroaniline derivatives and herbicidal compositions containing them

Country Status (6)

Country Link
US (1) US3332769A (en)
BE (1) BE661387A (en)
CY (1) CY488A (en)
DE (1) DE1542755C3 (en)
FR (1) FR1515830A (en)
GB (1) GB1071478A (en)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3403180A (en) * 1963-10-07 1968-09-24 Lilly Co Eli 4-trifluoromethyl-2, 6-dinitroanilines
USRE31226E (en) * 1963-10-07 1983-05-03 Eli Lilly And Company 4-Trifluoromethyl-2,6-dinitroanilines
USRE31227E (en) * 1963-10-07 1983-05-03 Eli Lilly And Company 4-Trifluoromethyl-2,6-dinitroanilines
US3764625A (en) * 1969-04-01 1973-10-09 United States Borax Chem Trifluoromethyl-1,3-phenylenediamine compounds
DE2013510C3 (en) * 1969-04-01 1985-11-14 United States Borax & Chemical Corp., Los Angeles, Calif. Use of 6-trifluoromethyl-2,4-dinitro-1,3-phenylenediamines as herbicides
US3764623A (en) * 1969-04-01 1973-10-09 United States Borax Chem Herbicidal dinitro-1,3-phenylenediamine compounds
US3716585A (en) * 1970-08-05 1973-02-13 United States Borax Chem Alkoxy trifluoromethylaniline compounds
US4251264A (en) * 1971-08-25 1981-02-17 American Cyanamid Company 2,6-Dinitroaniline herbicides
US3920742A (en) * 1971-08-25 1975-11-18 American Cyanamid Co N-sec-alkyl-2,6-dinitro-3,4-xylidine herbicides
US4165231A (en) * 1971-08-25 1979-08-21 American Cyanamid Company 2,6-Dinitroaniline herbicides
US4123250A (en) * 1972-04-19 1978-10-31 American Cyanamid Company Inhibiting plant bud growth with substituted 2,6-di-nitroanilines
US3991116A (en) * 1972-06-16 1976-11-09 Amchem Products, Inc. 4-Tert-butyl-N-sec-butyl-2,6-dinitroaniline
US4077795A (en) * 1972-08-22 1978-03-07 Union Carbide Corporation Method for inhibiting the growth of tobacco suckers
US3979453A (en) * 1975-06-23 1976-09-07 Eli Lilly And Company 3-Cyanamino-2,6-dinitroanilines
US4124639A (en) * 1975-12-22 1978-11-07 America Cyanamid Company N-alkoxyalkyl-2,6-dinitroaniline herbicides
US4101582A (en) * 1975-12-22 1978-07-18 American Cyanamid Company 2,6-Dinitroaniline herbicides
DE2728536A1 (en) * 1977-06-24 1979-01-11 Bayer Ag NEW 2-ARYLAMINO-3,5-DINITRO-BENZOTRIFLUORIDE
US4391992A (en) * 1979-08-24 1983-07-05 American Cyanamid Company N-Denitration of N,2,6-trinitroanilines with phase transfer catalysts
US5770545A (en) * 1997-03-14 1998-06-23 Srm Chemical, Ltd. Co. A2,6-dinitroaniline herbicide

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2947784A (en) * 1957-07-31 1960-08-02 Eastman Kodak Co Preparation of n, n-dibutyl aniline
BE571267A (en) * 1957-09-17
US3005026A (en) * 1958-07-17 1961-10-17 Dow Chemical Co N-substituted-2, 6-xylidines
US3067254A (en) * 1959-04-15 1962-12-04 Monsanto Chemicals N-(nitrophenyl) lower alkylcyclo-hexylamines
US3111403A (en) * 1960-08-31 1963-11-19 Lilly Co Eli Herbicidal method
US3088978A (en) * 1960-09-12 1963-05-07 Walter H Brunner Catalytic hydrogenation of 2, 4-dinitrophenylamines

Also Published As

Publication number Publication date
DE1542755A1 (en) 1970-07-23
DE1542755B2 (en) 1977-10-06
CY488A (en) 1969-04-29
FR1515830A (en) 1968-03-08
DE1542755C3 (en) 1978-06-01
US3332769A (en) 1967-07-25
BE661387A (en) 1965-09-20

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